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How To Recognize (and Solve) Wicked Content Strategy Problems [Rose-Colored Glasses]

Content strategy is a wicked problem.

Don’t worry. I didn’t adopt Bostonian lingo.

A wicked problem is hard to solve because of “incomplete, contradictory, or changing requirements that can be difficult to recognize.”

I like information researcher Jeff Conklin’s description of wicked problems as those “not understood until after the formulation of a solution.”

I see wicked problems a lot in content strategy. One of the toughest is recognizing why you need to change when you can’t see how things are broken.

One of the toughest things to recognize is why you should change when you can't see how things are broken, says @Robert_Rose via @CMIContent. Click To Tweet

Cooking up a wicked problem

My wife and I get around our kitchen just fine. We cook. The kitchen gets messy. We clean up and put things back where they go. We do the same thing at the next meal. It works fine for us.

Recently, a friend who came over for dinner wanted to help us cook. It was pure chaos. “Nothing is in the right place,” our guest said. She went to our junk drawer looking for silverware and opened our spice cabinet seeking plates. “Don’t even get me started with how the refrigerator is organized,” she said.

My wife responded, “This is how we’ve been doing this for years. It works for us.” Then I chimed in, “It’s the way we do it. It’s an optimized process.”

Our friend played along and said, “No. It’s the way you do it. But it’s not optimized.”

She was right. As she pointed out how things could be more efficient, we realized we had a problem.

A wicked problem.

In content strategy, experts often say documentation indicates a business’s commitment to its content. At its surface, a document seems oddly bureaucratic. How can creating a robust Google Doc or PowerPoint presentation be the lynchpin of a content strategy?

Spoiler alert: The document isn’t important.

However, having documentation means you’ve thought through the details of who’s responsible for what and how content works in and for your business.

Imagine how different our friend’s cooking experience would have been, for example, if we’d given her a detailed map of our kitchen and meal preparation workflow to review before her visit.

As the chef, she still could have pointed out the sub-optimal parts of our workflow and “asset management” strategy. But she also would have functioned better and, more importantly, could have seen where our kitchen organizational hacks made pragmatic sense.

It’s a lighthearted example, but it shows how documentation takes a lot of wickedness out of the problem.

#Content strategy documentation can take a lot of wickedness out of a problem, says @Robert_Rose via @CMIContent. Click To Tweet

Questions with no answers (yet)

About three months ago, I worked with a large, fast-growing technology company to roll out a new governance model, workflow, and content lifecycle management plan. The people who’d been with the company less than a year rejoiced. They loved it.

On the other hand, senior leaders and many veteran marketing and content practitioners didn’t. They agreed the solution sounded fine, but they didn’t see the problem it would solve.


I hear this question from CEOs and CFOs all the time: “I don’t see the problem. Tell me what’s the benefit of fixing it.”

The answer: We don’t know – yet.

Good people always lose to bad processes

Engineer and professor W. Edwards Deming once said, “If you can’t describe what you are doing as a process, you don’t know what you’re doing.”

What does that mean? For example, I can’t describe the process of writing this column every week, but I still get it done. I know what I’m doing.

But Deming doesn’t mean you don’t know what you’re doing. It’s that the organization doesn’t know what it’s doing.

For example, I talked about the technology company’s content creation process with the two global marketing practitioners responsible for translation and localization. I asked them to explain the process for how the hundreds of content pieces are selected, planned, and prioritized for distribution.

Here’s how they described it:

  1. They select articles based on gut feelings. Sometimes they have email conversations about the options, but sometimes whoever has time chooses the pieces.
  2. They list the chosen content on a spreadsheet, prioritizing each asset by highlighting it in red, yellow, or green.
  3. They upload the assets to an external file-sharing service because their internal digital asset management system doesn’t allow access by the agencies doing the translation and globalization.
  4. The agencies return the translated files to the two managers through the file-sharing service.
  5. The global marketing managers email the translated files to the local marketing managers in the correct regional offices.

How were other regional offices made aware of the content? How were the translated assets made centrally available? The two managers would upload them when they had time.

If those two managers left the business, the business would have a big ball of tangled translation and localization twine for the new person to unravel.

Cleaning the occurrent kitchen

Let’s return to the wicked challenge.

How can you answer the executives’ question about the potential value of fixing problems the business doesn’t know exists?

You can’t.

But you can develop a culture of examining occurrent behavior.

Occurrent behavior is what happens in the business vs. what is supposed to happen or what the business perceives is happening.

The technology company offers a great example. From the CMO’s perspective, nothing was broken. She perceived the operating model she inherited as working. When I showed her the translation and localization “process,” she said, “That’s not the way it was designed to work. But if it’s working, it’s working.”

Thousands of similar examples exist in every company. How people think things work differs from how they actually work. How many times have you onboarded an employee with advice like this: “This document says to email this department to get this answer, but just email Jane. She’ll get you the answer 10 times faster.”

Examine your content strategy ‘culture’

Stack up all that tacit knowledge, and it becomes the “culture.” Whether you conduct an audit, a review, or a simple set of experiments, really examine the occurrent behavior of your content strategy.

Here’s how to do it:

1. Figure out what’s going on

Develop a team to examine and document the occurrent behavior around your content – ideating, creating, managing, activating, publishing, promoting, measuring, and archiving.

If necessary, start with one area, such as marketing or thought leadership. Even better, start with one area of the customer’s journey. Document what happens (not what’s supposed to happen.) Identify and categorize the obvious challenges and where approaches go outside perceived models (even for good reason).

2. Plot the obvious gaps and inevitable costs

With the gaps documented, identify the costs, missed opportunities, or high-probability risks if they remain as is. For example, at the technology company, the siloed content creation process prompted employees to create new content rather than reuse content created from another silo. They found one e-book had 32 versions. What is the cost of the time spent on 31 unnecessary e-books?

3. Take a dragonfly view of estimating the challenge

Dragonflies see 360 degrees around them. People don’t. No one can develop a perspective that encompasses every aspect of every business process. But after looking at one area, you may be able to estimate the value of fixing your wicked problems based on the audits or experiments you’ve run.

Look at the costs for the obvious things (like the 31 extra e-books). Assume similar issues lie in other unexamined areas and extrapolate the costs. Include estimates based on what organizations similar to yours have found if you can.

Answer the value question

These steps should give you a helpful estimate of the value of developing or improving your strategic content processes.

People (and businesses) are reluctant to change, especially when they’re not feeling pain. But take heart. I’ve worked on more than 300 content strategy engagements and found companies that struggle to build a case for content strategy change end up finding the most success.

They’re already cooking, making meals, cleaning up, and succeeding, and they fear a change to that working routine will mess things up.

They’re not wrong to be reluctant. If they can’t understand the problem, looking at solutions can be confusing.

It’s a wicked problem.

But, if you don’t examine ways to improve incrementally, you’ll always have to fix things disruptively. You may not solve the wicked problem, but you might just pull enough wickedness out of them to be helpful.

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Cover image by Joseph Kalinowski/Content Marketing Institute